2008 Football League Cup final

As Premier League teams involved in UEFA competitions, both Chelsea and Tottenham entered the League Cup in the third round. Tottenham received a home draw against Middlesbrough, while Chelsea were drawn away to Hull City.[9] Chelsea won their tie 4–0; Scott Sinclair opened the scoring with his first goal for the club in the first half, while a brace from Salomon Kalou either side of another from Steve Sidwell completed the win.[10] Meanwhile, second-half goals from Gareth Bale and Tom Huddlestone sent Tottenham through to the next round.[11] Both teams were drawn at home in the fourth round; Chelsea would face Leicester City, while Tottenham would take on Blackpool.[12] Chelsea had to come from behind twice to beat Leicester; Frank Lampard had given them a 2–1 half-time lead after Gareth McAuley's early goal for Leicester, but DJ Campbell and Carl Cort put the visitors in front with two goals in the space of five second-half minutes. Andriy Shevchenko equalised for Chelsea in the 87th minute, before Lampard completed his hat-trick – and the Chelsea victory – in the final minute of the match.[13] For Tottenham, Robbie Keane opened the scoring in the first half against Blackpool; Pascal Chimbonda doubled the lead in the second half, and the away side were unable to find a response.[14] Chelsea were drawn at home again for the quarter-finals, this time against Liverpool, while Tottenham faced an away tie against Manchester City.[15] Tottenham took an early lead through Jermain Defoe in their quarter-final at the City of Manchester Stadium, but a red card for Didier Zokora in the 20th minute allowed City back into the game; however, Spurs secured victory and a place in the quarter-finals when Steed Malbranque scored in the 82nd minute.[16] The next day, Chelsea had to wait almost an hour to open the scoring against Liverpool at Stamford Bridge, Frank Lampard scoring his fourth goal of the competition; Peter Crouch was sent off for the visitors a minute later, and Shevchenko confirmed the win in the final minute.[17]

In the semi-finals, which would be played over two legs, Tottenham were drawn against their North London rivals Arsenal for the second season in a row, while Chelsea were paired with Everton, the city rivals of their opponents in the previous round.[18] Tottenham were held in their first leg at the Emirates Stadium, thanks to a deflected goal by Theo Walcott; after Jermaine Jenas opened the scoring for Spurs in the first half, Walcott equalised when the ball ricocheted back off him in the midst of a challenge by Lee Young-pyo before looping over Tottenham goalkeeper Radek Černý.[19] In the second leg at White Hart Lane, there was no doubt about the result, as Tottenham ran out 5–1 winners, their first victory over Arsenal in any competition since November 1999. Jenas was again on the scoresheet inside three minutes, before an own goal from Nicklas Bendtner gave Spurs a 2–0 half-time lead; Robbie Keane and Aaron Lennon doubled their advantage before Arsenal scored their first goal through Emmanuel Adebayor, but Malbranque scored in the final minute to secure a 6–2 aggregate victory.[20] Chelsea took the advantage in the first leg of their semi-final at Stamford Bridge despite John Obi Mikel's red card thanks to an own goal by Joleon Lescott in second-half injury time; Shaun Wright-Phillips opened the scoring midway through the first half, but Yakubu equalised in the 64th minute, only for Lescott to head a cross from Wright-Phillips into his own net.[21] In the second leg at Goodison Park, Joe Cole scored the only goal of the game in the 69th minute, giving Chelsea a 3–1 aggregate victory and sending them to their third League Cup final in the last four seasons.[22]

• Didier Drogba's goal made him the all-time leading scorer in League Cup Finals with four. He also became the first player to score in three League Cup finals and the first to score in three consecutive English domestic cup finals.